Lithium Hydroxide → Benzoic Acid

HRID 1976958Notes

Reaction equation

HRID 1976958 reaction equation
C[O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7](S(NCC2C=CC=C(OC(=O)C)C=2)(=O)=O)=[CH:6][C:5]=1Cl.[OH-].[Li+]>CO.O1CCCC1>[C:3]([OH:26])(=[O:2])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 54268702HCID 54268702, compound

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 4-[(3-acetoxybenzylamino)sulfonyl]-2-chlorobenzoic acid methyl ester (163 mg; 0.41 mmol) in methanol (3 mL) and tetrahydrofuran (3 mL) was treated at room temperature with an aqueous 1 N lithium hydroxide solution (1.65 mL). After 2 hr the volatiles were removed under reduced pressure and the residual material was dissolved in water (15 mL) and the solution filtered through Celite. The filtrate was acidified with 1 N HCl (2 mL) and extracted with ethyl acetate (3×10 mL). After the extracts were backwashed in turn with brine, they were combined, dried (Na2SO4) and evaporated in vacuo to furnish 140 mg of 2-chloro-4-[(3)-hydroxybenzylamino)sulfonyl]benzoic acid. A small sample of the product was crystallized from ethyl acetate-hexane to give a colorless solid, mp 167-169° C. FAB LRMS: (C14H12ClNO5S) Obs. Mass 342 Calcd. Mass 342 (M+H).

Workup

  1. customAfter 2 hr the volatiles were removed under reduced pressure
  2. dissolutionthe residual material was dissolved in water (15 mL)
  3. filtrationthe solution filtered through Celite
  4. extractionextracted with ethyl acetate (3×10 mL)
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-1f0ff906ca704a2b8be73c9b711c9ee8
Source dataset
uspto-grants-2001_05
Patent number
US06229011B1

Reaction notes

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